Potassium Hydroxide → 2'-(beta-D-glucopyranosyloxy)-6'-hydroxy-3-(5-benzo[b]furanyl)propiophenone

HRID 355343

反応式

HRID 355343 の反応式
C([O:4][C@@H:5]1[C@@H:10]([O:11]C(=O)C)[C@H:9]([O:15]C(=O)C)[C@@H:8]([CH2:19][O:20]C(=O)C)[O:7][C@H:6]1[O:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([OH:31])[C:26]=1[C:32](=[O:34])[CH3:33])(=O)C.[O:35]1[CH:39]=[CH:38][C:37]2[CH:40]=[C:41]([CH:44]=O)[CH:42]=[CH:43][C:36]1=2.[OH-].[K+].[TeH2].[Na].[Te].[BH4-].[Na+]>C(O)C>[C@@H:6]1([O:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([OH:31])[C:26]=2[C:32](=[O:34])[CH2:33][CH2:44][C:41]2[CH:42]=[CH:43][C:36]3[O:35][CH:39]=[CH:38][C:37]=3[CH:40]=2)[O:7][C@H:8]([CH2:19][OH:20])[C@@H:9]([OH:15])[C@H:10]([OH:11])[C@H:5]1[OH:4]

参加物

8

反応物 6

HCID 14797Potassium HydroxideHCID 27738751-Benzofuran-5-carbaldehydeHCID 4311764Sodium borohydrideHCID 6327182TelluriumHCID 105527942'-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyloxy)-6'-hydroxyacetophenoneHCID 131720910Sodium tellurium hydride

生成物 1

HCID 99331252'-(beta-D-glucopyranosyloxy)-6'-hydroxy-3-(5-benzo[b]furanyl)propiophenone収率 54%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒2 回

実験手順

To a mixture of 2'-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-6'-hydroxyacetophenone (965 mg), benzo[b]furan-5-carbaldehyde (350 mg) and ethanol (10 ml) is added dropwise a 50% aqueous potassium hydroxide solution (2 ml), and the mixture is stirred at room temperature overnight. The mixture is evaporated to remove the solvent, and to the residue are added water and diisopropyl ether. The mixture is stirred, and the aqueous layer is collected. The aqueous layer is neutralized with a 10% hydrochloric acid under ice-cooling, and extracted with ethyl acetate. The resulting organic layer is washed with water, dried, and evaporated to remove the solvent to give crude 2'-(β-D-glucopyranosyloxy)-6'-hydroxy-3-(5-benzo[b]furanyl)acrylophenone. This product is added to a solution of sodium tellurium hydride in ethanol (15 ml), which is previously prepared from tellurium (383 mg) and sodium borohydride (270 mg), and the mixture is reacted at room temperature for 2.5 hours. The insoluble materials are removed by filtration, and to the filtrate are added water and ethyl acetate. The mixture is stirred, and the organic layer is collected, washed with water, dried, and evaporated to remove the solvent. The residue is purified by silica gel column chromatography to give 2'-(β-D-glucopyranosyloxy)-6'-hydroxy-3-(5-benzo[b]furanyl)propiophenone (480 mg).

後処理

  1. customThe mixture is evaporated
  2. customto remove the solvent
  3. additionto the residue are added water and diisopropyl ether
  4. stirringThe mixture is stirred
  5. customthe aqueous layer is collected
  6. temperaturecooling
  7. extractionextracted with ethyl acetate
  8. washThe resulting organic layer is washed with water
  9. customdried
  10. customevaporated
  11. customto remove the solvent
  12. customto give crude 2'-(β-D-glucopyranosyloxy)-6'-hydroxy-3-(5-benzo[b]furanyl)acrylophenone
  13. customthe mixture is reacted at room temperature for 2.5 hours
  14. customThe insoluble materials are removed by filtration
  15. additionto the filtrate are added water and ethyl acetate
  16. stirringThe mixture is stirred
  17. customthe organic layer is collected
  18. washwashed with water
  19. customdried
  20. customevaporated
  21. customto remove the solvent
  22. customThe residue is purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-b95d04ede3654cd8ba5b5588accde24e
出典データセット
uspto-grants-1998_11
特許番号
US05830873

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